5'-Tosyladenosine

Base Information

• Chemical Name: 5'-Tosyladenosine
• CAS No.: 5135-30-8
• Molecular Formula: C17H19N5O6S
• Molecular Weight: 421.434
• Hs Code.: 29349990
• European Community (EC) Number: 225-883-1
• DSSTox Substance ID: DTXSID901276457
• Nikkaji Number: J80.959D
• Mol file: 5135-30-8.mol

Synonyms:5'-Tosyladenosine;5135-30-8;((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate;5'-O-Tosyladenosine;5'-O-(toluenesulfonyl)adenosine;5'-Tosyl Adenosine;MFCD00005751;5\'-Tosyl Adenosine;5'-O-(P-TOLUENESULFONYL)-ADENOSINE;5'-(toluenesulfonyl)adenosine;ADENOSINE 5?-TOSYLATE;5'-Tosyladenosine, >=99%;SCHEMBL4087758;DTXSID901276457;SRCA-00010;AC8834;AKOS025117354;AC-8700;CS-W016721;Adenosine, 5'-(4-methylbenzenesulfonate);AS-15634;5'-(4-Methylbenzenesulfonate) 2'-Deoxyadenosine;((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl4-methylbenzenesulfonate

Chemical Property of 5'-Tosyladenosine

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 151-153 °C
• Refractive Index: 1.6460 (estimate)
• Boiling Point: 760.1 °C at 760 mmHg
• PKA: 12.97±0.70(Predicted)
• Flash Point: 413.5 °C
• PSA: 171.06000
• Density: 1.75 g/cm³
• LogP: 1.40360
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 421.10560452
• Heavy Atom Count: 29
• Complexity: 670

Purity/Quality:

99% ^*data from raw suppliers

5’-TosylAdenosine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)OCC2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)O
• Isomeric SMILES: CC1=CC=C(C=C1)S(=O)(=O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)O
• Uses: 5'-Tosyladenosine is a compound useful in organic synthesis. Adenosine is a naturally occuring nucleoside and an essential building block in DNA synthesis. The tosyl protected adenosine at the 5' position, 5-tosyladenosine, allows for selective functionalistion at the the 3' and 4' positions, resulting in derivatised nucleotides that can incorporated into modified RNA which is an area of therapeutics that is currently expanding. 5’-Tosyl Adenosine (cas# 5135-30-8) is a compound useful in organic synthesis.

Technology Process of 5'-Tosyladenosine

There total 6 articles about 5'-Tosyladenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N6-benzoyl-5'-O-p-tolylsulphonyladenosine (127246-72-4) → 5'-tosyladenosine (5135-30-8)

Guidance literature:

With ammonia; In methanol; Ambient temperature;

DOI:10.1016/S0040-4020(01)89533-8

Reference yield:

N-benzoyladenosine (4546-55-8) → 5'-tosyladenosine (5135-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: aq. NH₃ / methanol

With pyridine; ammonium hydroxide; In methanol;

DOI:10.1039/b414739a

Reference yield:

p-toluenesulfonyl chloride (98-59-9) → 5'-tosyladenosine (5135-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: aq. NH₃ / methanol

With pyridine; ammonium hydroxide; In methanol;

DOI:10.1039/b414739a

upstream raw materials:

N⁶-benzoyl-5'-O-p-tolylsulphonyladenosine

p-toluenesulfonyl chloride

N-benzoyladenosine

Downstream raw materials:

5′-deoxy-5′-(4-methoxybenzylthio)adenosine

adenosine-5′-diphosphate trisodium salt

8-bromo-5'-O-(p-tolylsulfonyl)adenosine

5'-deoxyadenosine

Refernces

• 1、 Herdewijn, Piet. "REACTION OF ADENINE NUCLEOSIDES, TOSYLATED IN THE CARBOHYDRATE MOIETY, WITH LITHIUM TRIETHYLBOROHYDRIDE". . p. 6563 - 6580. Retrieved 2007/10/02.
• 2、 Schmidt,Schloz,Schwille. "Synthesis of 5'-modified adenosine derivatives". . p. 590 - 594. Retrieved 2007/10/08.